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The definition of the term derives from the practice of a small, occasionally used railway station signaling a train so the engineer will know to stop. Trains inbound to a "whistle stop" station would signal their approach with a blast of the train's steam whistle which would alert the train depot attendant to their arrival.[citation needed] If passengers, mail, or freight waited to be picked up at the depot, the depot master would raise a tower signal to indicate to the train engineer that the train should stop. If no stop was necessary, a different signal would be raised and the engineer could pass through the depot without a stop.[1]

One usage of the term in the political context, by Robert A. Taft, was derisive. He accused then-President Harry S Truman of "blackguarding Congress at whistle stops across the country".[2]

Use of the term has spread to cover any travel done very quickly and with only brief pauses. It is common to hear this expression in the United States, where the term originated, as well as the United Kingdom.

In the 19th century, when travel by railroad was the most common means of traveling long distances over the vast expanses of land as in the United States, politicians would charter tour trains which would travel from town to town. At each stop, the candidate would make a speech from the train, but might rarely set foot on the ground. "Whistle stop" campaign speeches would be made from the rear platform of a train.

One of the most famous railroad cars to be used in the U.S. whistle-stop tours was the Ferdinand Magellan, the only car custom built for the President of the United States in the 20th century. Originally built in 1928 by the Pullman Company and officially the "U.S. No. 1 Presidential Railcar", the Ferdinand Magellan is currently on display at the Gold Coast Railroad Museum in Miami, Florida. The famous news photo of Harry S Truman holding up a copy of the Chicago Tribune with a banner headline stating "Dewey Defeats Truman" was taken on this platform on Wednesday, November 3, 1948, at St. Louis Union Station. The Ferdinand Magellan was also used by President Franklin D. Roosevelt and, to a much lesser extent, by President Dwight Eisenhower. The Magellan’s last official trip before retirement was in 1954, when first lady Mamie Eisenhower rode it from Washington, D.C., to Groton, Connecticut, to christen the world’s first nuclear-powered submarine, the USS Nautilus. President Ronald Reagan used the Magellan for one day, October 12, 1984, traveling 120 miles in Ohio, from Dayton to Perrysburg, making five stops to give "whistle stop" speeches along the way.

Prince Charles of the United Kingdom started a five-day whistle-stop tour of the United Kingdom on Monday 6 September 2010 with a speech in Glasgow. The green campaigning tour is a part of the Prince's Start initiative that aims to build public awareness of sustainable activities. Indeed in Europe, touring politicians still occasionally take a train, as the excellent and still dense railway network offers access comparable to road travel and as it is better suited for extensive trips than air travel. In 2009 for example German chancellor (and CDU candidate) Angela Merkel made a highly publicized tour in Konrad Adenauer's old campaign train.[3] The SPD on the other hand only discontinued the use of train tours for campaign purposes ahead of the 1998 election.[4]